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B4: LIPIDS
FATS!!
General Info. - Lipids
   Organic molecules with long hydrocarbon
    chains
     Contains   oxygen, carbon, and hydrogen
   Soluble in non-polar solvents
     Organic   solvents
   Insoluble in water
   Occur in only 3 forms
B.4.1: Compare the composition of the 3
types of lipids found in the human body.

   3 types
     Triglycerides (aka fats and oils)
     Phospholipids (aka lecithin)

     Steroids (aka cholesterol)
B.4.1. (Triglycerides)
   Fat vs. Oil
     Fat  saturated (Solid)
     Oil  unsaturated (Liquid)

   Triglycerides are formed by
    CONDENSATION reaction between
    propane-1,2,3-triol (glycerol) and long chain
    carboxylic acids (fatty acids)
B.4.1. (Triglycerides)
   Can vary in length!
   Always EVENLY numbered in length!
B.4.1. (Phospholipids)
   Integral part of all cell membranes
   Made of four components
       GLYCEROL linked to TWO FATTY ACIDS and a PHOSPHATE
        GROUP by esterification; phosphate is linked to a NITROGEN
        CONTAINING ALCOHOL
B.4.2. (Phospholipids)




                           Fatty Acid Chain
                Glycerol
Choline Group
B.4.1. (Steroids)
   Also known as CHOLESTEROL
     HighDensity Lipid (HDL)
     Low Density Lipid (LDL)

   Organic structure of 4 rings (always have 20
    carbon atoms)
B.4.2: Outline the difference between HDL
and LDL cholesterol and outline its

   Both are LIPOPROTEINS
   Have SAME structure
   LDL transports CHOLESTEROL TO THE
    ARTERIES where it lines the walls.
     Saturatedfats
     Cardiovascular disease

   HDL can REMOVE cholesterol from the
    arteries and transport it back to the
B.4.3: Describe the difference in structure
between saturated and unsaturated fatty
   Saturated Fatty Acid
       Every carbon has the maximum amount of
        hydrogens (SINGLE bonds only)
   Unsaturated Fatty Acid
       DOUBLE bonds
           LOWER MELTING POINT
       Creates a “kink” or a bend
   STEARIC EFFECT (relevant to shape): the
    interjection of double bonded C atoms prevent
    the fatty acid molecules from approaching
    each other closely and hence interacting via
    Van der Waals’ forces.
B.4.3. (Saturated vs.
              SATURATED                                      UNSATURATED




   Type        Molec.
Structure      Phys.
Structure          Van
der
Waals            Mel7ng
Points
 Saturated    All
single
bonds
C‐C   Straight
chains          Greater
(more
        High
(solid
at
room

                                                       atoms)

stronger
interac9on        temp)

Unsaturated   One
C=C
(mono‐)
or
    Double‐bonds
            Lesser
(fewer
      Low
(liquid
at
room

              several
C=C
(poly‐)    à
kinked
chain    atoms)

weaker
interac9on        temp)
B.4.4: Compare the structures of the 2 essential
fatty acids linoleic (omega-6) and linolenic

    Linoleic (ω‐6
faJy
acid)
        POLY-UNSATURATED fatty acid
        Carboxylic acid with an 18 carbon chain and two cis-
         double bonds (C=C)
          cis means on the same side
        The first double bond is located at the 6th carbon from the
         methyl end (aka- the omega end) and the second is located
         at the 9th.

                                                   Carboxylic Acid
          omega end
B.4.4. (Linolenic (ω‐3
faJy
acid)
   POLY-UNSATURATED fatty acid
   Carboxylic acid with an 18 carbon chain and THREE cis- double
    bonds (C=C)
   The first double bond is located at the 3rd carbon from the
    methyl end (aka- the omega end), the second is located at the
    6th, and the third is located at the 9th. (Multiples of 3!)




                                                  Carboxylic Acid

     omega end
B.4.5: Define the term iodine number and
calculate the number of C=C double bonds in

     Unsaturated fats can undergo addition
      reactions
     One mole of Iodine reacts with one mole of
      double bonds
     Iodine is colored
     As reaction takes place, purple color
      disappears
     Fats can be described by their iodine
      number
B.4.5. (Calculating Iodine
   2 Titrations
     IBr and ICl mixed in glacial acetic acid  Iodine
      is formed (YELLOW)
     IBr and Icl mixed in glacial acetic acid + sample of
      FAT in solution
         Titrated w/ SODIUM THIOSULFATE
         Concentration of iodine is determined

   Difference of concentration of AMOUNT OF
    IODINE (in 2 titrations)
   Ratio of FAT: IODINE
B.4.6: Describe the condensation of
glycerol and 3 fatty acid molecules to

   Condensation     WATER is formed
   ESTERIFICATION between the glycerol
    backbone and 3 fatty acid molecules
   http://nutrition.jbpub.com/resources/
    animations.cfm?id=10&debug=0
   Requires 3 FATTY ACIDS +

 1 GLYCEROL
                             Glycerol (3 carbon
                             backbone)
B.4.6. (Formation of
B.4.7: Describe the enzyme-catalyzed
hydrolysis of triglycerides during
   Fats and oils are hydrolyzed by enzymes to
    GLYCEROL and FATTY ACIDS
   Enzymes known as LIPASES
   This is the REVERSE of the formation of fats
   After hydrolysis, the products are broken down
    further by a series of REDOX REACTIONS
   Produces CARBON DIOXIDE, WATER, and
    ENERGY
   Fats are in a LESS OXIDIZED form than
    carbohydrates so the same weight of fat
B.4.7. (Triglycerides during
B.4.8: Explain the higher value of fats as
compared to carbohydrates.
   Fats
     Long hydrocarbon chains
     Mass mainly from CARBONS (oxygen: carbon ratio
      small)
   Carbohydrates
     Contain EQUAL proportions of carbon and
      oxygen and TWICE AS MUCH HYDROGEN
      atoms
   Fats and Carbohydrates  metabolize
     CO2 and H2O (products)
B.4.8. (Reasoning for Higher
   Amount of OXIDATION that takes place as the
    compounds are converted to CO2 and H2O (Fat
    needs more oxidation to occur)
       In fats most carbons are bonded to hydrogen atoms, so
        when fats are metabolized they form more new C-O
        bonds, releasing more energy than carbohydrates
        (where C-O bonds exist)
       The bond enthalpy of the C-O bond is high, so when it
        forms a large amount of energy is released
   Fat molecules require about half as much
    oxygen for the same number of carbon atoms
       OXIDATION OF FATS IS LONGER, but produces more
        energy
B.4.9: Describe the important roles of lipids in
the body and the negative effects they can

      Cell Membranes (structurally)
        Phospholipids consist of a polar, hydrophilic
         phosphate ‘head’ and two hydrophobic fatty
         acid ‘tails’.
        Phospholipid will always point toward water
          creates the structure of the
         PHOSPHOLIPID BILAYER
      Energy Storage
        TRIGLYCERIDE    LIPIDS
B.4.9. (“Good” Roles of Lipids)
   Insulation and Protects Organs
     Adipose  tissue (ADIPOCYTES)
     Lipids are COVALENT COMPOUNDS that do
      not conduct heat or electricity easily.
   Steroid Hormones
     Cell-signaling

     HORMONE-PROTEIN        COMPLEXES + frequency
   Ω‐3
faJy
acids
reduce the risk of heart
    disease
     increasing   circulation and breaking down the
B.4.9. (“Bad” Roles of Lipids)
   Cholesterol + LDL
       A high-cholesterol diet can result in a high
        concentration of LDLs in the bloodstream
        (hardening and blocking)
   Obesity
     Carbohydrates not metabolized as turned into
      lipids via adipocytes (leading to increased body
      mass)
     Increased body mass leads to strains on other
      body parts

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Lipids: Structure, Types and Functions in the Body

  • 2. General Info. - Lipids  Organic molecules with long hydrocarbon chains  Contains oxygen, carbon, and hydrogen  Soluble in non-polar solvents  Organic solvents  Insoluble in water  Occur in only 3 forms
  • 3. B.4.1: Compare the composition of the 3 types of lipids found in the human body.  3 types  Triglycerides (aka fats and oils)  Phospholipids (aka lecithin)  Steroids (aka cholesterol)
  • 4. B.4.1. (Triglycerides)  Fat vs. Oil  Fat  saturated (Solid)  Oil  unsaturated (Liquid)  Triglycerides are formed by CONDENSATION reaction between propane-1,2,3-triol (glycerol) and long chain carboxylic acids (fatty acids)
  • 5. B.4.1. (Triglycerides)  Can vary in length!  Always EVENLY numbered in length!
  • 6. B.4.1. (Phospholipids)  Integral part of all cell membranes  Made of four components  GLYCEROL linked to TWO FATTY ACIDS and a PHOSPHATE GROUP by esterification; phosphate is linked to a NITROGEN CONTAINING ALCOHOL
  • 7. B.4.2. (Phospholipids) Fatty Acid Chain Glycerol Choline Group
  • 8. B.4.1. (Steroids)  Also known as CHOLESTEROL  HighDensity Lipid (HDL)  Low Density Lipid (LDL)  Organic structure of 4 rings (always have 20 carbon atoms)
  • 9. B.4.2: Outline the difference between HDL and LDL cholesterol and outline its  Both are LIPOPROTEINS  Have SAME structure  LDL transports CHOLESTEROL TO THE ARTERIES where it lines the walls.  Saturatedfats  Cardiovascular disease  HDL can REMOVE cholesterol from the arteries and transport it back to the
  • 10. B.4.3: Describe the difference in structure between saturated and unsaturated fatty  Saturated Fatty Acid  Every carbon has the maximum amount of hydrogens (SINGLE bonds only)  Unsaturated Fatty Acid  DOUBLE bonds  LOWER MELTING POINT  Creates a “kink” or a bend  STEARIC EFFECT (relevant to shape): the interjection of double bonded C atoms prevent the fatty acid molecules from approaching each other closely and hence interacting via Van der Waals’ forces.
  • 11. B.4.3. (Saturated vs. SATURATED UNSATURATED Type Molec.
Structure Phys.
Structure Van
der
Waals Mel7ng
Points Saturated All
single
bonds
C‐C Straight
chains Greater
(more
 High
(solid
at
room
 atoms)

stronger
interac9on temp) Unsaturated One
C=C
(mono‐)
or
 Double‐bonds
 Lesser
(fewer
 Low
(liquid
at
room
 several
C=C
(poly‐) à
kinked
chain atoms)

weaker
interac9on temp)
  • 12. B.4.4: Compare the structures of the 2 essential fatty acids linoleic (omega-6) and linolenic  Linoleic (ω‐6
faJy
acid)  POLY-UNSATURATED fatty acid  Carboxylic acid with an 18 carbon chain and two cis- double bonds (C=C)  cis means on the same side  The first double bond is located at the 6th carbon from the methyl end (aka- the omega end) and the second is located at the 9th. Carboxylic Acid omega end
  • 13. B.4.4. (Linolenic (ω‐3
faJy
acid)  POLY-UNSATURATED fatty acid  Carboxylic acid with an 18 carbon chain and THREE cis- double bonds (C=C)  The first double bond is located at the 3rd carbon from the methyl end (aka- the omega end), the second is located at the 6th, and the third is located at the 9th. (Multiples of 3!) Carboxylic Acid omega end
  • 14. B.4.5: Define the term iodine number and calculate the number of C=C double bonds in  Unsaturated fats can undergo addition reactions  One mole of Iodine reacts with one mole of double bonds  Iodine is colored  As reaction takes place, purple color disappears  Fats can be described by their iodine number
  • 15. B.4.5. (Calculating Iodine  2 Titrations  IBr and ICl mixed in glacial acetic acid  Iodine is formed (YELLOW)  IBr and Icl mixed in glacial acetic acid + sample of FAT in solution  Titrated w/ SODIUM THIOSULFATE  Concentration of iodine is determined  Difference of concentration of AMOUNT OF IODINE (in 2 titrations)  Ratio of FAT: IODINE
  • 16. B.4.6: Describe the condensation of glycerol and 3 fatty acid molecules to  Condensation  WATER is formed  ESTERIFICATION between the glycerol backbone and 3 fatty acid molecules  http://nutrition.jbpub.com/resources/ animations.cfm?id=10&debug=0  Requires 3 FATTY ACIDS + 1 GLYCEROL Glycerol (3 carbon backbone)
  • 18. B.4.7: Describe the enzyme-catalyzed hydrolysis of triglycerides during  Fats and oils are hydrolyzed by enzymes to GLYCEROL and FATTY ACIDS  Enzymes known as LIPASES  This is the REVERSE of the formation of fats  After hydrolysis, the products are broken down further by a series of REDOX REACTIONS  Produces CARBON DIOXIDE, WATER, and ENERGY  Fats are in a LESS OXIDIZED form than carbohydrates so the same weight of fat
  • 20. B.4.8: Explain the higher value of fats as compared to carbohydrates.  Fats  Long hydrocarbon chains  Mass mainly from CARBONS (oxygen: carbon ratio small)  Carbohydrates  Contain EQUAL proportions of carbon and oxygen and TWICE AS MUCH HYDROGEN atoms  Fats and Carbohydrates  metabolize  CO2 and H2O (products)
  • 21. B.4.8. (Reasoning for Higher  Amount of OXIDATION that takes place as the compounds are converted to CO2 and H2O (Fat needs more oxidation to occur)  In fats most carbons are bonded to hydrogen atoms, so when fats are metabolized they form more new C-O bonds, releasing more energy than carbohydrates (where C-O bonds exist)  The bond enthalpy of the C-O bond is high, so when it forms a large amount of energy is released  Fat molecules require about half as much oxygen for the same number of carbon atoms  OXIDATION OF FATS IS LONGER, but produces more energy
  • 22. B.4.9: Describe the important roles of lipids in the body and the negative effects they can  Cell Membranes (structurally)  Phospholipids consist of a polar, hydrophilic phosphate ‘head’ and two hydrophobic fatty acid ‘tails’.  Phospholipid will always point toward water  creates the structure of the PHOSPHOLIPID BILAYER  Energy Storage  TRIGLYCERIDE LIPIDS
  • 23. B.4.9. (“Good” Roles of Lipids)  Insulation and Protects Organs  Adipose tissue (ADIPOCYTES)  Lipids are COVALENT COMPOUNDS that do not conduct heat or electricity easily.  Steroid Hormones  Cell-signaling  HORMONE-PROTEIN COMPLEXES + frequency  Ω‐3
faJy
acids
reduce the risk of heart disease  increasing circulation and breaking down the
  • 24. B.4.9. (“Bad” Roles of Lipids)  Cholesterol + LDL  A high-cholesterol diet can result in a high concentration of LDLs in the bloodstream (hardening and blocking)  Obesity  Carbohydrates not metabolized as turned into lipids via adipocytes (leading to increased body mass)  Increased body mass leads to strains on other body parts